Reaktion #45323

Reaktionsgleichung

methyl [3,5-bis(trifluoromethyl)benzyl][(4-iodo-5′-isopropyl-2′-methoxybiphenyl-2-yl)methyl]carbamate

CuCN

Water

→

title compound

Methyl [3,5-bis(trifluoromethyl)benzyl][(4-cyano-5′-isopropyl-2′-methoxybiphenyl-2-yl)methyl]carbamate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with EtOAc (3×15 ml)
2. 2
   WaschenThe combined EtOAc layers were washed with brine
3. 3
   Trocknendried over sodium sulfate

Vorschrift

A mixture of methyl [3,5-bis(trifluoromethyl)benzyl][(4-iodo-5′-isopropyl-2′-methoxybiphenyl-2-yl)methyl]carbamate from Example 10 (0.03 g, 0.045 mmol) and CuCN (0.008 g, 0.09 mmol) in DMF (1 ml) was stirred at 100° C. overnight. Water (10 ml) was added and the mixture was extracted with EtOAc (3×15 ml). The combined EtOAc layers were washed with brine, and dried over sodium sulfate. The title compound was obtained after preparative thin layer chromatography using 2:8 EtOAc/hexane as the eluant. 1H NMR (CDCl3, 500 MHz) δ 7.72 (s, 1H), 7.74 (m, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.49 (m, 1H), 7.38 (m, 1H), 7.36 (d, J=8.0 Hz, 1H), 7.28 (m, 1H), 6.94 (d, J=2.5 Hz, 1H), 6.91 (m, 1H), 4.26-4.49 (m, 4H), 3.81 (m, 3H), 3.70 (s, 3H), 2.92 (m, 1H), 1.22 (s, 6H). LC-MS (M+1) 565.3 (4.42 min).

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